2-Methyl-3-butyn-2-ol → 3-((4-Acetylpiperazin-1-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575256Notes

Reaction equation

HRID 575256 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[N:15]3[CH2:16][CH2:17][O:18][C:19]4[CH:24]=[CH:23][C:22](Br)=[CH:21][C:20]=4[C:14]3=[N:13][C:12]=2[C:26]([NH2:28])=[O:27])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].BrC1C=CC2OCCN3C(CN4CCCC4)=C(C(N)=O)N=C3C=2C=1.N1(C(=O)C)CCNCC1.[CH3:62][C:63]([OH:67])([C:65]#[CH:66])[CH3:64]>>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[N:15]3[CH2:16][CH2:17][O:18][C:19]4[CH:24]=[CH:23][C:22]([C:66]#[C:65][C:63]([OH:67])([CH3:64])[CH3:62])=[CH:21][C:20]=4[C:14]3=[N:13][C:12]=2[C:26]([NH2:28])=[O:27])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 837951-AcetylpiperazineHCID 8669325310-Bromo-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 866932673-((4-Acetylpiperazin-1-yl)methyl)-10-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 866932663-((4-Acetylpiperazin-1-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 42%

Procedure

Similar to as described in General Procedure G, 3-((4-acetylpiperazin-1-yl)methyl)-10-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide (prepared similarly as described in the synthesis of 10-bromo-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide replacing pyrrolidine with 1-(piperazin-1-yl)ethanone) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a colorless solid (34 mg, 42%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-a75ea9a5d3d441fdaf793bf004790021
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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